58 Randolph Rd, Brookline, MA 02467
Property image
Property image
OFF MARKET

58 Randolph Rd
Brookline, MA 02467

Chestnut Hill
  • 4 Beds
  • 4 Baths
  • 4,845 sqft (on 0.31 acres)

$3,590,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $21,270/mo*
Refinance Your Home

$3,590,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $21,270/mo*
Refinance Your Home
4 Beds
4 Baths
4,845 sqft
(on 0.31 acres)

Home Value

Trulia Estimate
$3.59M
Since last month
Decreased$66K (-1.8%)
Since last year
Increased$184K (+5.4%)
Since last sale
Increased$1M (+46.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +65% in the last 10 years
MonthEstimated value
2026
August 2026$3.6M
July 2026$3.66M
June 2026$3.71M
May 2026$3.67M
April 2026$3.6M
March 2026$3.61M
February 2026$3.5M
January 2026$3.44M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
59 Randolph Rd, Brookline, MA
0.03
Single-Family Home
$2,950,000
06/26/26
4
3.5
3,230
35 Jefferson Rd, Brookline, MA
0.02
Single-Family Home
$2,245,000
09/08/25
5
3.5
3,634
76 Norfolk Rd, Brookline, MA
0.13
Single-Family Home
$2,325,000
12/04/25
3
3
2,486
98 Spooner Rd, Brookline, MA
0.45
Single-Family Home
$3,300,000
06/15/26
4
4.5
3,628
167 Willard Rd, Brookline, MA
0.59
Single-Family Home
$3,400,000
09/23/25
4
3.5
3,298
25 Chestnut Hill Rd, Newton, MA
0.71
Single-Family Home
$2,200,000
07/29/26
4
3.5
2,800
46 Malia Ter, Newton, MA
0.47
Single-Family Home
$3,036,350
10/06/25
5
4.5
3,909
401 Clinton Rd, Brookline, MA
0.83
Single-Family Home
$2,200,000
06/15/26
5
3.5
3,463
47 Nancy Rd, Newton, MA
0.70
Single-Family Home
$2,250,000
10/30/25
3
2.5
2,844
23 Crafts Rd, Brookline, MA
0.15
Single-Family Home
$5,100,000
10/03/25
7
8
7,140

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
35 Jefferson Rd, Brookline, MA 02467
0.02
$2,325,400
5
3.5
3,634
Off Market
5 Jefferson Rd, Brookline, MA 02467
0.08
$2,993,800
3
4
4,543
Off Market
37 Randolph Rd, Brookline, MA 02467
0.05
$2,996,400
5
4.5
3,430
Off Market
42 Jefferson Rd, Brookline, MA 02467
0.03
$4,156,400
5
6
5,658
Off Market
59 Randolph Rd, Brookline, MA 02467
0.03
$2,950,000
4
3.5
3,230
Recently Sold
76 Norfolk Rd, Brookline, MA 02467
0.13
$2,325,000
3
3
2,486
Recently Sold
1014 Boylston St, Brookline, MA 02467
0.08
$16,980,000
7
9.5
13,343
For Sale
409 Heath St, Brookline, MA 02467
0.07
$3,576,500
5
3.5
3,500
Off Market
19 Crafts Rd, Brookline, MA 02467
0.13
$4,555,500
5
5.5
6,995
Off Market
401 Heath St, Brookline, MA 02467
0.07
$2,689,100
5
3.5
3,819
Off Market
23 Crafts Rd, Brookline, MA 02467
0.15
$5,212,000
7
8
7,140
Off Market
331 Heath St, Brookline, MA 02467
0.11
$3,750,000
3
3.5
3,790
For Sale

Local Information

  • Map ViewExplore the area around 58 Randolph Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1928
Lot Size
0.31 acres
Living Area
4,845 sqft
Price/Sqft
$741
Parking
Garage

About this House

Set on beautifully manicured grounds in Chestnut Hill, this stunning residence, with high ceilings, many windows, and hardwood floors, has been meticulously updated. The expansive main level features an oversized living room with a fireplace; a four-season sunroom; a custom kitchen with a breakfast bar, a pantry, top-of-the-line appliances; and a elaborate family room with a cathedral ceiling, custom details, wall of windows, and a door opening to the backyard. A dining room, an office, a half bathroom, a porch, and access to the two-car garage complete this level. The second floor is comprised of a private master bedroom with a full bathroom and ample closet space, three other large bedrooms, a full bathroom, and laundry. The lower level, with direct outdoor access, has a play room and a family room. Amenities include radiant heat and updated air-conditioning and gas systems. This property is in the Heath School district, close to The Street, "T" station, and Route 9.
58 Randolph Rd, Brookline, MA 02467 is a 4 bedroom, 5 bathroom, 4,845 sqft single-family home in Chestnut Hill, built in 1928. It last sold for $2,450,000 on Mar 6, 2020. It is currently off market. The Trulia Estimate is $3,590,300, with a rent estimate of $8,398/month.

Home Details for 58 Randolph Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: SlateExterior: StuccoPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1928Year Updated: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Price and Tax history

DateEventPrice
Mar 6, 2020
Source: N/A
Sold
$2,450,000
Jan 21, 2020
Source: Agent Provided
Listed For Sale
$2,495,000
Nov 9, 2016
Source: N/A
Sold
$2,100,000
Sep 23, 2016
Source: Agent Provided
Pending
$2,250,000
Jul 11, 2016
Source: Agent Provided
PriceChange
$2,250,000
Price decreased by 2%

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

Neighborhood Overview

Chestnut Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Chestnut Hill

At least 41 Trulia users voted on each feature.

  • 91 % Say there are sidewalks

  • 86 % Say it's dog friendly

  • 81 % Say car is needed

  • 73 % Say they plan to stay for at least 5 years

  • 71 % Say yards are well-kept

  • 71 % Say streets are well-lit

  • 70 % Say there's holiday spirit

  • 66 % Say parking is easy

  • 66 % Say people would walk alone at night

  • 63 % Say it's walkable to restaurants

  • 63 % Say kids play outside

  • 62 % Say it's quiet

  • 57 % Say there's wildlife

  • 55 % Say there are community events

  • 53 % Say it's walkable to grocery stores

  • 44 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Dma333
    "Diverse, safe, close to everything, friendly neighbors, great schools, playgrounds in walking distance"
    0
    Flag
  • Steve L.
    "Hancock Village in Chestnut Hill is a good place to live overall. Sometimes the management office puts together special functions like handing out cider doughnuts in the fall, or flowers to plant - both gratis. (And more as well but too much to detail)."
    4
    Flag
  • Dma333
    "Block party in September Close to a great school Playgrounds nearby Diverse community Easy access to many communities "
    1
    Flag
  • Szonja.ruppert
    "Lots of greens, parks, even bags for dogpoop is put to parks. Not many pet shops in walking distance"
    0
    Flag
  • Jawaher A.
    "Good schools, no stealing, good neighbors, good place to kids to play, not far away from BU university, there is driving school, all government facilities around us, Uber so expensive but it is available all time, there is ice cream shop and Starbucks around us also a lot of restaurants and malls "
    2
    Flag
  • Jawaher A.
    "I love this area coz its safe and beautiful and the neighbors are nice and kind and there is a lot of great people "
    0
    Flag
  • Fish r.
    "Lovely neighborhood that's close to anything and everything -- shopping, restaurants, movies, doctors, gyms, public transportation, Soule recreation center & golf course, etc. Very safe, with lots of places to go for peaceful walks. I have lived here for nearly two decades and love it."
    5
    Flag
  • Jacquizieff
    "It an a upscale and snobby neighborhood where people don’t talk to each other. We never see kids and kids make no friends in the neighborhood. Clean safe closet To Boston. Nothing around. No walking distance to anything. Supermarket and gas is over priced. "
    0
    Flag
  • Robert B.
    "Wooded neighborhood surrounded by open space on 3 sides - farm stand and parks nearby. Safe, easy commute, great schools."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 58 Randolph Rd

  • What is 58 Randolph Rd estimated to be worth?
    Trulia's estimated value for 58 Randolph Rd in Brookline, MA is $3,590,300.
  • What is the price history for 58 Randolph Rd?
    58 Randolph Rd in Brookline, MA last sold for $2,450,000 in March 2020.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • Does 58 Randolph Rd have air conditioning?
    Yes, 58 Randolph Rd in Brookline, MA has air conditioning.
  • How big is the lot at 58 Randolph Rd?
    The lot at 58 Randolph Rd in Brookline, MA is about 0.31 acres (13,503 sq ft).

Explore by feature - Pet Friendly

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